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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

A photograph of Father Douglass visiting the School in 1928. The photograph shows Father Douglass, Rev Scriven, Rev Edward Vere Hodge, Rev Frank Jerwood, Helen Hodge and Walter Lee Sargant in front of the Chapel.

Oakham School Magazine, recording the Spring term 1929 (published in Summer term 1929). Contents: Frontispiece; Editorial; School Notes; The Captain of the Ship; To G.H.; The Prefect's Lot; Extracts from a Wanderer's Diary; Boxing and Fencing Club; The Sports, Cricket; O.T.C.; O.O. News; Correspondence; Games Accounts. The name 'Worthington' is hand-written on the cover. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1892 (published in Summer term 1892). Contents: Editorial; School Notes; Presentation to the Rev F.W. Douglass; The Plantin Museum, Antwerp; A Live Stock Dealer; Poetry; In Memoriam; The Late Rev Robert Wade-Gery; The Debating Society; Paperchase; The Athletic Sports; Football; Correspondence. Nine double-pages A to I.

The Oakhamian Magazine, recording the Summer term 1949 (published in Winter term 1949). Contents: School News; Play Reading Society; Music Notes; Frederick Wingfield Douglass; C.C.F.; Scout Notes; Cub Notes; Field Society; Photographic Society; Stamp Society; Railway Society; Geography Society; Debating Society; Museum; Austria; Cricket; Swimming Sports; Steeplechases; Hodge Wing Christmas Show; Ruby Football; Sparks from the Torch; O.O. News; Correspondence. Item belonged to D.J. Stocks. Seven double-pages A to G.

The Oakhamian Magazine, recording the Spring term 1952 (published in Summer term 1952). Contents: School News; C.C.F.; Shooting; Scout Notes; Cub Notes; Geographical Society; Music Notes; Art Society; Field Society; Cricket; Swimming; Junior Sports; Boxing; Speech Day; The Antigone; Sparks from the Torch; Father Douglass of Behala; Football Fixtures; Correspondence; O.O. News; Oxford Letter; Cambridge Letter. Eight double-pages A to H.

The Oakhamian Magazine, recording the Winter term 1955 (published in Spring term 1956). Contents: School News; Avete; Valete; House Transfers; Spencer Leeson; C.C.F.; Shooting; Scout Notes; Cub Notes; Chess; Debating Society; Film Notes; The Twenty-One Club; Philatelic Society; Lectures; Sparks from the Torch; O.P.R.S. Notes; Music; The Medals of Father Douglass; Christmas Crackers; Rugby Football; John Haywood; Hockey; Under 14 Football; Cross Country Running; The Mile; Junior Steeplechase; Athletics Match; Boxing; The Sports; Cricket Fixtures; O.O. News. Eight double-pages A to H.

Oakham School Magazine, recording the Spring term 1895 (published in Summer term 1895). Contents: Editorial; School Notes; The Gymnasium; The Debating Society; Swimming; Statement of a Bengali Pleader at Barisal; Horace; The Sports; Cricket. Six double-pages A to F.

The Oakhamian Magazine, recording the Winter term 1981 and Spring term 1982. Contents: Editorial; Letters to the Editors; School News; O.O. News; Prize Winning Essay; Interview; A Distinguished Oakhamian; Profile; Hoax!; Creative Writing; Music; Drama; Sports; School Officials.